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US7423110B2 - Polysulfone compositions exhibiting very low color and high light transmittance properties and articles made therefrom - Google Patents

Polysulfone compositions exhibiting very low color and high light transmittance properties and articles made therefrom Download PDF

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US7423110B2
US7423110B2 US10/511,094 US51109405A US7423110B2 US 7423110 B2 US7423110 B2 US 7423110B2 US 51109405 A US51109405 A US 51109405A US 7423110 B2 US7423110 B2 US 7423110B2
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polysulfone
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US20050176923A1 (en
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Mohammad Jamal El-Hibri
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Solvay Specialty Polymers USA LLC
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/06—Polysulfones; Polyethersulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses

Definitions

  • This invention is directed to a polysulfone composition with low yellowness index and high light transmittance and articles made from the polysulfone composition, such as ophthalmic lenses.
  • Sulfone polymers are high performance amorphous thermoplastic engineering resins that contain the characteristic diaryl sulfone linkage. Sulfone polymers are known for their high mechanical strength, thermal and oxidative resistance, resistance to hydrolysis, and to many acids, bases, and solvents.
  • Polysulfone is a well-known high temperature amorphous engineering thermoplastic resin. It exhibits a high glass transition temperature of about 185° C., high strength, stiffness and toughness over a temperature range from about ⁇ 100 to 150° C. Being completely amorphous, the polymer also exhibits transparency, which adds to its utility in many end uses. Polysulfone was commercially introduced in 1965 by the Union Carbide Corporation. It has the chemical structure:
  • polysulfone shown above commonly abbreviated as PSU
  • PSU polysulfone
  • polyarylethers aromatic backbone polymers
  • These polymers can be produced by a variety of methods.
  • U.S. Pat. Nos. 4,108,837 and 4,175,175 describe the preparation of polyarylethers and in particular polyarylethersulfones.
  • Several one-step and two-step processes are described in these patents, which patents are incorporated herein by reference in their entireties.
  • a double alkali metal salt of a dihydric phenol is reacted with a dihalobenzenoid compound in the presence of sulfone or sulfoxide solvents under substantially anhydrous conditions.
  • a dihydric phenol is first converted, in situ, in the presence of a sulfone or sulfoxide solvent to the alkali metal salt derivative by reaction with an alkali metal or an alkali metal compound.
  • the starting monomers are bisphenol A and a 4,4′-dihalodiphenylsulfone, typically 4,4′-dichlorodiphenylsulfone.
  • the bisphenol A is first converted to the dialkali metal salt derivative by first reacting with a base like sodium hydroxide, NaOH, in a 1:2 stoichiometric molar ratio to produce the disodium salt of bisphenol A.
  • This disodium salt of bisphenol A is then reacted with 4,4′-dichlorodiphenylsulfone in a second step to produce the polymer.
  • Sodium chloride salt is produced as a byproduct of the polymerization
  • the salt is filtered, then the polymer solution is either contacted with a non-solvent to precipitate the polymer or, alternatively, the polymer is recovered by evaporative removal of the solvent. In either case, the solvent removal is usually followed by forming of the polymer into pellets in an extruder, preferably a twin screw extruder.
  • this polymer is transparent in its natural state.
  • the transparency of polysulfone is useful in combination with its high heat and other high performance attributes. Examples of uses where the transparency is useful include covers and lids for hot serving dishes and containers, lids for medical sterilization trays, research lab animal cages, dairy processing equipment, flow meters and sight glasses for chemical process equipment.
  • polysulfone is therefore particularly attractive for use in ophthalmic lenses for spectacles used in prescription eyewear.
  • Water white or near water white clarity is a key requirement for any lens material, and, to date, the state of the art of polysulfone manufacture has not yet allowed the production of resin with the type of clarity that is needed.
  • Polysulfone has been of interest to the ophthalmic lens industry for a long time as it offers a number of attractive features.
  • polysulfone offers low cost thermoplastic lens fabrication methods (i.e. hybrid injection-compression molding).
  • the good impact resistance of polysulfone allows thin lenses to be viable.
  • Yellowness index and color factor are two different quantities from the standpoint of the definition of the parameter. However, for practical purposes, they do correlate very well.
  • x and y are the chromaticity coordinates obtained by normalizing the X and Y tristimulus values.
  • the variable t is the sample thickness in inches. So, unlike YI, CF is independent of thickness in the thickness range of typical molded components, which is one attractive aspect of the quantity. Color factor is independent of thickness up to about 1 inch thick.
  • the 270 factor is an arbitrarily chosen factor intended primarily to bring the CF values into a convenient range to work with.
  • yellowness index, light transmittance and haze are all thickness dependent properties so that thickness needs to be reported along with these measurements.
  • multiple thicknesses should be measured to show the dependence of these properties on thickness over a practical range of thicknesses.
  • a color factor target of ⁇ 10 has been set for plastic molded parts to be considered of optical quality. This corresponds, in yellowness index terms (ASTM D-1925) to yellowness index of ⁇ 1.9 for a 0.1 inch thick sample plaque.
  • the lowest color factors achieved in molded articles of prior art commercially produced polysulfone have been in the 30-40 color factor range and more typically they have been in the 50-70 range.
  • PSU with solution batch color factors of under 25 has been produced based on improvements in PSU manufacture technology as described for, example, by Schwab et al. in U.S. Pat. No. 4,307,222, which is incorporated herein by reference in its entirety, the ability to produce melt fabricated articles with color factors of less than 25 has not been demonstrated.
  • FIG. 1 This plot shows the progression of color factor of two polysulfone batches. Samples of the polysulfone powder were heat aged in a melt indexer at 300° C. and various times to monitor the dependence of color factor on 300° C. exposure time. It can be seen from FIG. 1 that even after 2 minutes at 300° C., both polysulfone samples approximately double in color factor, and after 12 minutes the color factor has risen to roughly 3 ⁇ the original value. This behavior is disconcerting, considering that 300° C. is at the lower limit of where polysulfone can realistically be melt fabricated by injection molding.
  • FIG. 2 is a graph showing the correspondence between CF and YI for a number of UDEL® lots as measured on plaques 0.1 inch thick.
  • the relationship between the two variables is essentially a straight line that passes through the origin.
  • the corresponding yellowness index on a 0.1 inch thickness specimen is closely approximated by multiplying CF by 0.19.
  • the straight line relationship between CF and YI shows how the color factor measurement relates to the more widely used yellowness index parameter.
  • a polysulfone composition having a total luminous light transmittance of 84% or greater when measured on 0.1 inch thick specimens using ASTM D-1003.
  • YI yellowness index
  • CF color factor
  • YI yellowness index
  • CF color factor
  • a polysulfone composition comprising a polysulfone, an organic phosphorous containing melt stabilizer, and at least one of the following additives: a blue to violet dye and an organic optical brightener.
  • an optical component such as an ophthalmic lens having a yellowness index less than 1.00.
  • the stabilizer Sandostab PEPQ is used at loading levels of about 750 ppm. Trace amounts of a violet to blue dye and/or an optical brightener can also be used to offset, either completely or partly, remaining yellowness in the resin. Color factors as low as 11 with low haze, high transmittance and good overall aesthetics have been achieved on molded plaques based on embodiments of this invention.
  • the present invention addresses the longstanding limitation of yellowing in polysulfone thereby allowing modified compositions that reach the clarity levels needed for lens applications to be possible for the first time.
  • the present invention enables, for the first time, the production of nearly colorless polysulfone with high light transmittance characteristics over the visible spectrum.
  • FIG. 1 graphically illustrates the progression of the color factor of polysulfone upon exposure to 300° C.
  • FIG. 2 graphically illustrates the correspondence between color factor and yellowness index as measured on 0.1 inch thick plaques.
  • FIG. 3 graphically illustrates transmittance dependence on color factor as measured on 0.1 inch thick plaques.
  • FIG. 4 graphically contrasts the transmittance of polysulfone and polycarbonate.
  • FIG. 5 graphically illustrates the visible transmittance spectra of polysulfone with various color stabilization additives according to the instant invention.
  • FIG. 6 graphically illustrates the dependence of Yellowness Index on sample plaque thickness.
  • the present invention enables the production of molded polysulfone articles with improved light transmittance and reduced yellowing.
  • the present invention provides lightweight, high-light transmittance ophthalmic lenses.
  • the present invention allows the high temperature handling and molding of polysulfone without the attendant decrease in light transmittance and increased yellowing observed in prior art polysulfone compositions. These benefits are provided by a polysulfone composition comprising small amounts of additives selected from organic phosphorous-containing melt stabilizers, optical brighteners, and blue to violet dyes.
  • This invention relates to bisphenol A polysulfone compositions that are very low in color and yellowness and high in light transmittance over the visible spectrum. Color factors below 20 have been achieved as compared to color factors in the 30-40 range being possible previously from commercially available polysulfone. At color factors below about 20 (yellowness index less than about 4.0 at a 0.10′′ sample thickness) a resin becomes a candidate for use in optical components. Certain embodiments of this invention comprise bisphenol A polysulfone to which is added 30 to 3000 ppm of an organic phosphite and/or organic phosphonite, and, additionally contains either
  • compositions of the instant invention comprise 100 to 1000 ppm of the organic phosphite and/or organic phosphonite, and, additionally contain either:
  • Additional embodiments of the present invention consist of a polysulfone and an organic phosphite and/or organic phosphonite, and, additionally either:
  • Polysulfones used in the practice of this invention can be of any practical molecular weight to afford melt processability and good physical and mechanical properties.
  • the number average molecular weight for the PSU is greater than 13,000 g/mole. In other embodiments of the present invention the number average molecular weight is greater than 15,000 g/mole as measured by gel permeation chromatography using methylene chloride as the solvent and polystyrene calibration standards.
  • the resins of this invention In order to allow for melt processing at temperatures as low as possible it is also desirable for the resins of this invention to have melt flow rates of at least 7 g/10 min as measured according to ASTM method D-1238 at a temperature of 343° C. and a load of 2.16 kg.
  • the melt flow rate of the PSU will be at least 10 g/10 min and in other certain embodiments, at least 15 g/10 min at the conditions stated.
  • compositions comprising copolymers of polysulfone fall within the scope of the invention.
  • copolymers in which the bisphenol portion of the reactants in the condensation polymerization is comprised of at least 75 mole % bisphenol A and up to 25% of (an)other bisphenol(s), such as bisphenol S (4,4′-dihydroxydiphenylsulfone), bisphenol O (4,4′-dihydroxydiphenylether), biphenol (4,4′-dihydroxydiphenyl), or hydroquinone (C 6 H 4 (OH) 2 ).
  • bisphenol portion of the reactants in the condensation polymerization is comprised of at least 75 mole % bisphenol A and up to 25% of (an)other bisphenol(s), such as bisphenol S (4,4′-dihydroxydiphenylsulfone), bisphenol O (4,4′-dihydroxydiphenylether), biphenol (4,4′-dihydroxydiphenyl), or hydroquinone (C 6 H 4 (OH) 2
  • the organic phosphorous-containing melt stabilizers suitable for use in the practice of this invention can be from the phosphite or phosphonite family or mixtures thereof Suitable phosphites that include mono and dialkyl substituted aromatic phosphites.
  • the phosphites are di-t-butyl substituted aromatic phosphites, such as tris(2,4di-t-butyl-phenyl) phosphite.
  • suitable phosphites include those containing the pentaerythritol moiety.
  • Aromatic phosphonites are also suitable in certain embodiments of this invention, particularly aromatic mono and diphosphonites.
  • a particularly suitable phosphonite is tetrakis(2,4di-tert-butylphenyl)[1,1-biphenyl]-4,4′-diylbisphosphonite.
  • this phosphonite is used in combination with a phosphite from the above described phosphites.
  • the phosphonite used in combination with the phosphonite is tris(2,4t-butylphenyl)phosphite. In such mixtures the phosphonite is preferred to be the major component and the phosphite the minor one.
  • a stabilizer composition which fits this description is sold commercially under the trademark Sandostab PEPQTM. Sandostab PEPQTM has been found to be particularly well-suited for use in the practice of this invention.
  • polysulfones with the lowest color factors available commercially have been in the 30-40 color factor range and more typically they have been in the 50-70 range.
  • This invention introduces polysulfone color factors approaching 10, making polysulfone a serious candidate in optical lens applications for the first time in its history.
  • a first set of experiments examined the potential benefits of eight additive system scenarios on inhibiting polysulfone color development during melt processing.
  • the additives were compounded using a 25 mm Berstorff twin screw extruder at a melt temperature of about 325° C.
  • Various compositions according to the present invention are listed in Table 1.
  • the stabilized samples were compared for their optical properties with a virgin control and a ‘blank’ extruded control to separate the effect of the compounding heat history from the role played by the additives.
  • the samples were injection molded (at about 325° C. melt temperature) to produce 0.10′′ color plaques which were tested for color factor, yellowness index, haze, and luminous light transmittance, which according to ASTM D-1003 is the same as the Y component of the tristimulus values.
  • Weston 618TM is a pentaerythritol based phosphite available from General Electric Specialty Chemicals, Inc.
  • PEPQTM is a mixture of a phosphite and phosphonites available from Clariant Corp.
  • Irgafos 168TM is a phosphite available from Ciba Specialty Chemicals, Inc.
  • HP-136TM is a lactone-based melt stabilizer available from Ciba Specialty Chemicals, Inc.
  • the structure of Weston 618TM, Sandostab PEPQTM, Irgafos 168TM, and HP-136TM are shown in Tables 2 and 3.
  • compositions were compounded on a Berstorff 25 mm twin screw extruder using mild conditions (melt temperature ⁇ 325° C.). They were molded into 0.1 inch (2.5 mm) thick color plaques also using mild melt temperature of ⁇ 325° C. Details of the experiments and results are presented below.
  • Other organic phosphites and/or phosphonites can also be used in the practice of this invention, as would be clear to one of ordinary skill in this art.
  • suitable organic phosphites include Dover Chemical's Doverphos S-9228TM.
  • compositions were compounded in 15 pound lots.
  • the compositions were compounded at a temperature profile so that a melt temperature of about 325° C. was achieved.
  • the conditions were kept as near constant as possible for all runs.
  • the compositions were run at a throughput rate of about 30 lb/hr and an RPM of about 200.
  • the temperature settings of the extruder are listed in Table 6.
  • UDEL® P-3703 NT polysulfone had a color factor of about 30 before dusting.
  • compositions in Table 8 were dusted, dried, then injection molded into color plaques (2′′ ⁇ 3′′ ⁇ 0.10′′) using an Arburg 75 ton machine and mild processing conditions (melt temp. ⁇ 325° C.).
  • Optical properties were measured on the color plaques and these included the following: color factor, haze, light transmittance, X, Y, Z tristimulus coordinates, yellowness index, and a light transmittance vs. wavelength profile. Results are fully documented herein.
  • the PEPQTM was combined with 2 ppm ZIRS Oil VioletTM, and in another embodiment, it was combined with 25 ppm of Eastobrite OB-3TM optical brightener which is a molecule designed to absorb light in the near UV range and transmit it in the visible.
  • Eastobrite OB-1TM and Eastobrite OB-3TM comprise the same optical brightener compound as described in Table 3, however, the OB-3TM composition additionally contains a small amount of a blue dye preblended into it by the supplier.
  • These compositions were again prepared using “dusting” as a means of incorporating the additives into the resin as opposed to compounding.
  • compositions comprised pellets that have been dusted with the target levels of each of the powderous additives.
  • a master batch of PSU and additive is prepared using a conventional compounding extruder to produce pellets of PSU containing the additives at higher than (e.g. 5-10 times) their desired concentration levels according to this invention.
  • the pellets of the master batch are then tumble blended with virgin PSU pellets and injection molded or extruded or otherwise melt fabricated into their final form.
  • a 10 ppm master batch blend was prepared first because that is much easier to prepare/control than a 2 ppm composition.
  • Example 10 the amount of dye was reduced down to the level of Example 10 composition using 20% by weight master batch and the balance polysulfone and whatever was needed to complete the composition including PEPQTM. This approach ensured more homogeneous incorporation of the violet dye into the resin prior to injection molding. It is important that the resins with dusted stabilizer are dried thoroughly in a desiccated oven prior to injection molding. Injection molding procedures similar to those used for molding Examples C2-C7 and Examples 1-6 were used for molding Examples 7-12 and control C9. Control C10 was molded according to commonly known guidelines for injection molding polycarbonate resin.
  • Eastobrite OB-1 and OB-3TM optical brighteners improve the transmittance of the polysulfone compositions.
  • the combination of PEPQTM with ZIRS Oil VioletTM or Eastobrite OB-3TM causes an additional 5 unit reduction in the color factor (from 21 to 16) without any significant increase in haze. While the color factors of Examples 10 and 12 are about the same, the light transmittance profiles are different. This can be seen in FIG. 5 where the transmittance curves of Control C9 and Examples 7, 10, and 12 are overlaid. The individual light transmittance values are recorded in Table 12.
  • VR 40 melt stability tests were run to determine to what extent the melt stability of the polysulfone may be jeopardized by the addition of additives employed. The results of the VR 40 melt stability tests were all favorable, as can be seen in Table 11, with very little viscosity change over the 40-minute test duration at 410° C.
  • an optical brightener Eastobrite OB-3TM
  • Eastobrite OB-3TM was also found effective in reversing resin yellowness and producing a similar neutralization of the resin's residual yellow cast.
  • a color factor of 16 was also achieved using the combination of PEPQTM at 750 ppm with OB-3 at 25 ppm.
  • the PEPQTM, ZIRS dye and OB-3TM can all be used together as a ternary combination, to synergistically reduce the levels required of each of the ZIRS and OB-3 additives. While counteracting yellowness, it was found that the Eastobrite OB-3TM optical brightener boosts the transmittance by about 2% in the 440-700 nm wavelength range but causes absorption in the 400-440 nm range.
  • additives required for the practice of this invention can include but are not limited to: lubricants, mold releases, antistatic agents, UV absorbers, flame retardants, anti-fogging agents and matting agents.
  • the color factor was measured on 0.1′′ thick plaques and a color factor of 24 was recorded, which represents an almost 50% reduction relative to the control.
  • the yellowness index, light transmittance and haze were measured at all four thicknesses and the values are reported in Tables 13-15.
  • the yellowness index of the resin can be reduced substantially through the use of the instant invention.
  • the yellowness index is reduced by approximately a factor of two in going from the control case to the case of comparative example C12, and a three to four fold reduction in yellowness index is achieved with the practice of the invention as illustrated in Example 13.
  • the reduction in yellowness index is achieved without any significant loss in light transmittance and without any increase in haze levels, as shown in Tables 13-15. As such, all three aspects of a good optical quality material: low yellowness index, high light transmittance and low haze are achieved simultaneously.
  • the yellowness index (YI) data from control C11, comparative example C12 and Example 13 are plotted as a function of thickness in FIG. 6 .
  • the YI data falling at the origin of the plot is also considered to be a requirement and a constraint on the YI-thickness correlation due to the removal of all color absorbing quality in the materials at the limit of vanishing thicknesses.
  • the YI data plotted in FIG. 6 show that the YI is related to thickness by a simple straight line relationship.
  • the straight line equations going through the origin for each of the three cases illustrated are listed on the graph in FIG. 6 . From these straight line proportionality relationships, interpolated estimates for the thicknesses corresponding to any given YI can be calculated.
  • the yellowness index is linearly related to the thickness of the molded article.
  • Table 16 transparent, molded polysulfone articles with yellowness indices less than 1.00, 0.75, and 0.50 are included within the scope of this invention.
  • Certain embodiments of the present invention also include molded optical components, such as ophthalmic lenses, with yellowness indices less than 1.00, 0.75, and 0.50.
  • transparent layers of polysulfone having yellowness indices less than 1.00, 0.75, and 0.50 are included within the scope of this invention.
  • molded polysulfone articles with color factors less than 5, 4, and 3 are included within the scope of this invention.
  • Certain embodiments of the present invention also include molded optical components, such as ophthalmic lenses, with color factors less than 5, 4 and 3.
  • transparent layers of polysulfone having color factors less than 5, 4, and 3 are included within the scope of this invention.
  • polysulfone is conventionally formed by reacting 2,2-bis(4-hydroxyphenyl)propane (also known as bisphenol A) with at least one diarylsulfone compound.
  • Polycarbonate grade bisphenol A is a high purity grade of bisphenol A and is commercially available from several manufacturers. Polycarbonate grade bisphenol A is used to make polysulfone and optical quality polycarbonate.
  • polycarbonate grade bisphenol A typically comprises trace amounts isomeric impurities, such as 2-(4-hydroxyphenyl)-2-(2-hydroxyphenyl)propane (the ortho/para isomer) and 2,2-bis(2-hydroxyphenylpropane (the ortho/ortho isomer).
  • Commercially available polycarbonate grade bisphenol A typically contains less than 0.27% by total weight of the ortho/para and ortho/ortho isomers.
  • commercially available polycarbonate grade bisphenol A contains less than 0.15% by total weight of the ortho/para and ortho/ortho isomers.
  • polycarbonate grade bisphenol A that contains less than 200 ppm of the ortho/para and ortho/ortho isomers is commercially available.
  • Optical components within the scope of this invention include non-ophthalmic lenses, prisms, waveguides, optical fibers, lighting fixtures, and electronic devices.
  • the instant disclosure encompasses a wide variety of embodiments not specifically illustrated herein.

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PCT/US2003/011501 WO2003089519A1 (fr) 2002-04-15 2003-04-15 Compositions de polysulfone presentant une couleur tres faible et des proprietes de transmittance elevees et articles fabriques a partir de ces compositions

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US20070123692A1 (en) 2007-05-31
US20050176923A1 (en) 2005-08-11
US20050003661A1 (en) 2005-01-06
JP4393201B2 (ja) 2010-01-06
ES2298514T3 (es) 2008-05-16
ATE382071T1 (de) 2008-01-15
CN1659235A (zh) 2005-08-24
DE60318308T2 (de) 2009-03-05
KR20040108736A (ko) 2004-12-24
EP1497375B1 (fr) 2007-12-26
JP2005522574A (ja) 2005-07-28
WO2003089519A1 (fr) 2003-10-30
US7662909B2 (en) 2010-02-16
KR100996377B1 (ko) 2010-11-24
US7169702B2 (en) 2007-01-30
DE60318308D1 (de) 2008-02-07
AU2003230919B2 (en) 2009-04-09
AU2003230919A1 (en) 2003-11-03
EP1497375A1 (fr) 2005-01-19
CN100448933C (zh) 2009-01-07

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